N-chloro-succinimide; dodecyl-methyl-sulphide; triethylamine in dichloromethane T=-40°C; Corey-Kim oxidation; 14 h;

diisobutylaluminium hydride in hexane; toluene T=-78°C; 15-20 min;

1: 95 percent / K2CO3 / dimethylformamide / 1.5 h / 150 °C 2: 96 percent / lithium aluminum hydride / tetrahydrofuran / 3 h / 60 °C 3: 96 percent / pyridinium chlorochromate / tetrahydrofuran / 3 h / 20 °C View Scheme

1: 1.) potassium carbonate, dimethylsilyl dichloride / 1.) DMF, RT, 1 d, 2.) DMF, 2 d 2: 87 percent / potassium carbonate / dimethylformamide / 48 h 3: 90 percent / hydrazinum hydroxide / acetone / 18 h / Heating 4: 93 percent / pyridine / 0 - 20 °C 5: 64 percent / sodium carbonate / ethane-1,2-diol / 75 h / 160 °C View Scheme

1: HCl 2: NaOH 3: K2CO3 / KI 4: 4.25 g / LiAlH4 / tetrahydrofuran / 0.5 h 5: 3.9 g / active MnO2 / CHCl3 / 0.5 h / Heating View Scheme

1: 92 percent / K2CO3 / dimethylformamide / 1 h / 110 °C 2: 95 percent / LiAlH4 / tetrahydrofuran / 0.67 h / 25 °C 3: 90 percent / MnO2 / CH2Cl2 / 2 h / 25 °C / other reagent View Scheme

1.1: dioxane / 24 h / 20 °C 1.2: 64 percent / HCl / dioxane / 24 h / 20 °C 2.1: 94 percent / pyridine / 0.25 h / 0 °C 3.1: 61 percent / phenyliodine(III) bis(trifluoroacetate) / 2,2,2-trifluoro-ethanol / 0.17 h / -40 °C 4.1: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 5.1: 83 percent / pyridine / 3 h / 0 °C 6.1: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 7.1: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 8.1: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 9.1: NaBH4 / methanol / 24 h / 20 °C View Scheme

1.1: dioxane / 24 h / 20 °C 1.2: 64 percent / HCl / dioxane / 24 h / 20 °C 2.1: 94 percent / pyridine / 0.25 h / 0 °C 3.1: 61 percent / phenyliodine(III) bis(trifluoroacetate) / 2,2,2-trifluoro-ethanol / 0.17 h / -40 °C 4.1: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 5.1: 83 percent / pyridine / 3 h / 0 °C 6.1: 98 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 72 h / 60 °C 7.1: 78 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 3 h / -78 °C 8.1: 96 percent / TBAB; KOH / methanol / 24 h / 80 °C 9.1: NaBH4 / methanol / 24 h / 20 °C 10.1: 46.3 mg / 48 h / Heating 11.1: 94 percent / lithium aluminum hydride / tetrahydrofuran / 7 h / 20 °C View Scheme

1: methanol / 1.17 h / 70 °C 2: 5.5 g / NaBH4 / methanol / 1.17 h / 0 - 20 °C 3: 97 percent / 6 h / Heating 4: 35.5 percent / phenyliodine(III) diacetate / 0.67 h / 20 °C 5: 95 percent / BCl3 / CH2Cl2 / 20 h / -78 °C 6: 98 percent / pyridine / 1 h / 0 °C 7: 97 percent / formic acid; Et3N; PPh3 / Pd(OAc)2 / dimethylformamide / 3 h / 60 °C 8: lithium tri-sec-butylborohydride / tetrahydrofuran / 6 h / -78 °C 9: 23.4 mg / lithium aluminum hydride / tetrahydrofuran / 12 h / 20 °C View Scheme

in tetrahydrofuran; hexane T=25°C; 1.5 h;